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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Pleasant Valley holiday homes

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

1. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is £316
includes taxes & fees
28 Sept - 29 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

2. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is £401
includes taxes & fees
29 Sept - 30 Sept
Amazing 3-bedroom house with AC in adorable Highland
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

3. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is £191
includes taxes & fees
30 Sept - 1 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

4. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is £206
includes taxes & fees
28 Sept - 29 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

5. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is £98
includes taxes & fees
29 Sept - 30 Sept
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

6. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is £639
includes taxes & fees
4 Oct - 5 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

7. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"The pictures are misleading"
United States
Jia
The price is £210
includes taxes & fees
28 Sept - 29 Sept
The Studio at the Inn at High Falls
A spacious living area with a staircase, a dining table, and a sofa.

8. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is £543
includes taxes & fees
29 Sept - 30 Sept
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

9. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

10. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (4 reviews)
"Very convenient and welcoming. Perfect place for a quick stop over."
United States
Jenna H.
The price is £196
includes taxes & fees
19 Oct - 20 Oct
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

11. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View
Highland
The price is £723
includes taxes & fees
1 Oct - 2 Oct
Hudson Escape W/ Hot Tub + Bridge View
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is £217
includes taxes & fees
28 Sept - 29 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A hot tub on a wooden deck with a view of a river and trees.

13. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is £383
includes taxes & fees
12 Oct - 13 Oct
Welcome to The Boathouse! Waterfront/Boats/Hot tub
An outdoor patio area with a covered seating area, a pool, and potted plants.

14. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is £262
includes taxes & fees
30 Sept - 1 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

15. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (103 reviews)
"Wonderful stay. "
United States
Chris L.
The price is £207
includes taxes & fees
28 Sept - 29 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A room with a bed, a couch, a desk with a computer, and various wall decorations.

16. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is £211
includes taxes & fees
28 Sept - 29 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

17. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is £367
includes taxes & fees
28 Sept - 29 Sept
Historic Cottage * Steam Shower * Chef’s Kitchen
A deck with wicker furniture and a view of a lake at sunset.

18. Many perfect sunsets at the magical house on the lake

Many perfect sunsets at the magical house on the lake
Ulster Park
9.8 out of 10, Exceptional, (156 reviews)
"Highly recommend!"
United States
Seth M.
The price is £441
includes taxes & fees
1 Oct - 2 Oct
Many perfect sunsets at the magical house on the lake
A covered outdoor area with a barbecue grill and a hot tub.

19. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (40 reviews)
"Exactly as listed, great property and host."
United Kingdom
Neil C.
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

20. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
Retro Retreat: renovated 2BR, desk, no chore list!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasant Valley Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good
"This is a cost-effective option for the region. The rooms are clean, but the motel has a run-down feel to it. When we arrived, the card-key generator wasn't working. Staff let us in to our room, and we got working keys the next morning, but I haven't run into that problem anywhere else. Likewise, the card-reader on a side entrance, which would have been very useful for accessing our room, was broken, necessitating a longer walk around to the front of the motel. In the shower, the plate behind the dial had come away from the wall. It didn't affect the quality of the shower (which was fine in terms of heat and pressure), but it's not a good look. Breakfast was good and plentiful (I had scrambled eggs and sausages, but there's also cereal, various breads, and a waffle-maker, with orange and apple juice). My wife and I would come back, and thus the "Good" overall rating."
Robert 2-night trip
Posted less than an hour ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Find out more about Pleasant Valley

Pleasant Valley Holiday Homes information

Number of reviews
541
Accommodation
373 Holiday Homes
Lowest Price
£98
Highest Price
£723